Should you or should you not risk it?

Today I saw a quote attributed to Erica Jong: “If you don’t risk it, you risk even more.”


As someone raised in an environment of high certainty (study hard, go to uni, get a degree, get a good job, work till you retire), the transition to self-employment was especially difficult.

13 years after leaving the legal profession and 7 years into working for myself, I still have moments when I wonder: what if I hadn’t made that momentous decision to quit?

Would I be just as fulfilled being a lawyer? (Who knows?)

Would I get restless again further down the road? (Probably.)

Would I be financially more stable? (Definitely, or at least until I stumble on that magic formula for entrepreneurial success.)

The should-I-risk-it dilemma has no easy answers, since we can only live one life at a time, and saying yes to one decision often means saying no to other opportunities that may turn out to be just as ‘good’.

The only guarantee is that time will continue to pass whether we put off the day of decision, or decide that TODAY is the day we write a new chapter in our life.

So then the question becomes: if I were to look back on this day 20 years from now, would I regret not taking the risk, or would I regret having tried and failed?

For me, the answer has always been that I will regret not finding out for myself what else I am capable of, and what possibilities are out there. That was what drove me to throw away a perfectly good career and the privilege of writing “lawyer” as my occupation on questionnaires. My inner adventurer has an insatiable need for variety and challenge, especially when there has been too much certainty and predictability.

What would make it worth it for you to take the risk?


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